One of the most lucrative and profitable occupations was that of the Medieval Innkeeper, but only if all conditions were prime and if certain circumstances were maintained.
Anyone who could afford the structure and property could embrace the free enterprise of having an Inn, however he or she was subject to heavy taxes and levies by the local lords of the area.
Owning an Inn carried a lot of responsibility. Besides the bedrooms the Inn also had other internal features such as a dining rooms and often a tavern or alehouse. Usually the fare for a room included meals as well. The alehouse was sometimes leased by a secondary business person and often a separate enterprise from the Inn.
Cleaning, maintaining and providing quality goods and services were the primary requirements of an Innkeeper. One also had to be good with mathematics and money and even have the presence of mind to calculate bookings and the ordering of supplies and inventory. Most times an Innkeeper hired a small staff of armed security guards. It was not uncommon for a group of fighters to arrive at an Inn shortly after their latest campaign. Rowdy and hoping to spend the spoils of war, the atmosphere inside most Inns and alehouses could be bawdy and even at times violent.
At the doorway to an Inn you could find at least one armed guard posted. There was usually a minimal entry fee to pass through the door, just a courtesy to help pay for any damages that may arise while inside. The guard at the door would take a brass or copper coin from the entrant and bounce it on a wet piece of wood. If the coin bounced once it was clear that the coin was genuine and the person was allowed to enter. Many times people would forge their own coins out of lead or cheaper metals and since Europe saw a wide variety of foreign money, it was often difficult to prove the authenticity of a coin. The practice of bouncing the coin off of a wet piece of wood is what eventually led to modern day doormen at bars and pubs being called "Bouncers".
Many times nobles and elite personnel were exempt from paying any fees at an Inn or hostel. Though this was resented by most Innkeepers, they did receive fair protection in return. If the business was maintained properly, an Innkeeper could earn high profits.

INTERPRETER

Interpreters earned excellent wages despite whom they worked for. There was a scarcity of people versed in more than one language and as a result, Interpreters were highly sought after by kings and monarchs. Not only did an Interpreter serve to reveal information about captured foreign troops, but also he could compose letters, laws and doctrines that helped with the subjugation of foreign territories.
Also it was necessary throughout the Medieval Ages to hold meetings, conversations and diplomatic gatherings with nobles and ruling members of many foreign countries. Therefore the Interpreter held an elite position and was often given rank, land and titles in exchange for his or her valuable services.

JESTER

The Jester seldom had an easy job. Though some were professionals and made their livings touring from kingdom to kingdom, most were forced into the position as an act of humiliation.
King Henry V often enjoyed taking captured Knights of elite title and rank and forcing them to play the fool before his entire court. If the Jester was successful at entertaining his troops and guests, he would be hauled back to the dungeons after his performance to live to do it again another day. If the Jester did not provide gleeful entertainment he was often tortured or killed.
Jesters lived precariously and often their success depended solely on the mood of their audience. They did not earn high wages but were often allowed a few benefits and luxuries of life inside a castle.